Upcoming Events
Embrace the allure of our Eastern Shore haven, where each passing season ushers in its own tapestry of charm and adventure! As we peer into the unfolding year, we're excited to present exciting happenings and unforgettable moments. Whether you're drawn to the vibrant hues of spring's awakening, the spirited festivities of summer's peak, the rustic warmth of autumn's embrace, or the magical enchantment of winter's frost, there's an experience tailored to enchant every soul. Navigate below to find the ideal time to plan your stay.
Summer 2025
Independence Day
Join us for a star-spangled celebration with the best seats in town! Settle into our cozy waterfront Adirondack chairs—or take to the water aboard one of our elegant vessels—for a truly unforgettable view of St. Michaels’ dazzling fireworks display.
July 5th Fireworks Cruise:
Group Charter | 8–10 PM | $185 per person
*Charters include bubbly and sweet treats. Tax and gratuity additional.
Rum Running on the Skipjack
Join us every Wednesday from 5:30–7:00 PM starting July 9th for an evening of sailing, storytelling, and handcrafted tastings from our friends at LYON Rum . This adventure is timed perfectly to catch a front-row view of the Wednesday Night Sailboat Races on the Miles River. Visit our Fleet page to learn more!
Plein Air Easton
Plein Air Easton, celebrating its 21st year July 11 - 20 2025, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.
CBMM Waterman’s Appreciation Day & Crab Feast
Mark your calendars for August 10th as the Chesapeake Bay Maritime Museum comes to life with the Waterman’s Appreciation Day & Crab Feast. Pair these nautical spectacles with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat! Visit here to read about the history and importance of the Chesapeake Bay Watermen.
Fall 2025
Chesapeake Film Festival
The prestigious Chesapeake Film Festival returns to Easton, Maryland from October 10th - 12th! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought-provoking documentaries, and engaging discussions with industry experts.
Fall into St. Michaels
Fall into the enchantment of St. Michaels October 17 - 19! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.
Oyster Fest
Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 25th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!
Waterfowl Festival
Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 14th - 16th! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!
Eastern Shore Sea Glass & Coastal Arts Festival: Holiday Edition
Mark your calendar for November 22nd, as the Chesapeake Bay Maritime Museum in St. Michaels, Maryland, hosts the Holiday Edition of the beloved Sea Glass and Coastal Arts Festival. This seasonal celebration will showcase coastal craftsmanship at its finest, with over 90 exhibitors offering unique jewelry, home décor, art, and more—just in time for the holidays.
